Artemether supplier | CasNO.71963-77-4

Name
Artemether
EINECS 663-549-0
CAS No. 71963-77-4
Article Data13
CAS DataBase
Density 1.18 g/cm³
Solubility
Melting Point 86-89oC
Formula C₁₆H₂₆O₅
Boiling Point 357.5 °C at 760 mmHg
Molecular Weight 298.379
Flash Point 140.5 °C
Transport Information OTH
Appearance
Safety 24/25
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
Synonyms Albendazole Oral Suspension;SM 224;Artemetero [INN-Spanish];beta-Dihydroartemisinin methyl ether;Artemether [INN];3,12-Epoxy-12H-pyrano[4,3-j]-1,2- benzodioxepin,decahydro-10-methoxy-3,6,9- trimethyl-,(3R,5aS,6R,8aS,9R,10S,12R,12aR)-;Coartem;Methyl-dihydroartemisinine;Artemetherum [INN-Latin];3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin, decahydro-10-methoxy-3,6,9-trimethyl-;beta-Artemether;Methyl-ether-qinghaosu;[3R-(3.alpha.,5a.beta.,6.beta.,8a.beta.,9.alpha.,10.alpha.,12.beta.,12aR*)]-Decahydro-10-methoxy-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4.3-j]-1,2-benzodioxepin;Artemisininelactol methyl ether;Artemisinin ,Artemether99%;
PSA 46.15000
LogP 2.84080

Synthetic route

: 1445-45-0
Trimethyl orthoacetate

: 71939-50-9
dihydroartemisinin

: 71963-77-4
artemether

Conditions

Conditions	Yield
With perchloric acid In ethanol at 0℃; for 8h; pH=2; Reagent/catalyst; pH-value; Temperature;	97.6%

: 24823-81-2
trimethoxypropane

: 71939-50-9
dihydroartemisinin

: 71963-77-4
artemether

Conditions

Conditions	Yield
With sulfuric acid In isopropyl alcohol at 0 - 12℃; for 4h; pH=2; Solvent; Temperature; Reagent/catalyst; pH-value;	97.2%

: 71939-50-9
dihydroartemisinin

: 149-73-5
trimethyl orthoformate

: 71963-77-4
artemether

Conditions

Conditions	Yield
With methanesulfonic acid In ethanol at 5 - 20℃; for 3h; pH=5; Solvent; pH-value; Temperature; Reagent/catalyst;	96.6%
toluene-4-sulfonic acid In methanol at 30℃; for 0.5h;

: 67-56-1
methanol

: 81496-81-3
dihydroartesiminin

: 71963-77-4
artemether

Conditions

Conditions	Yield
With dimethylphosphoric acid; boron trifluoride diethyl etherate at 3 - 20℃; Reagent/catalyst; Temperature;	96.2%

: 81496-81-3
dihydroartesiminin

: 149-73-5
trimethyl orthoformate

: 71963-77-4
artemether

Conditions

Conditions	Yield
Stage #1: dihydroartesiminin; trimethyl orthoformate In methanol at 20℃; for 0.25h; Stage #2: With acetyl chloride In methanol at 10 - 15℃; Stage #3: With sodium hydrogencarbonate In methanol; water at 0 - 5℃; for 2h; Product distribution / selectivity;	74.67%

: 3976-69-0
Methyl (R)-3-hydroxybutyrate

: 71939-50-9
dihydroartemisinin

A: 82596-30-3
9,10-dehydrodihydroartemisinin

B: 71963-77-4
artemether

C: 120020-67-9
C20H32O7

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In diethyl ether for 24h; Ambient temperature;	A n/a B n/a C 70%

...Expand

: 53562-86-0
(S)-3-hydroxybutyric acid methyl ester

: 71939-50-9
dihydroartemisinin

A: 82596-30-3
9,10-dehydrodihydroartemisinin

B: 71963-77-4
artemether

C: 119946-74-6
C20H32O7

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In diethyl ether for 24h; Ambient temperature;	A n/a B n/a C 56%

...Expand

: 67-56-1
methanol

: 71939-50-9
dihydroartemisinin

A: 71963-77-4
artemether

B: α-artemether

Conditions

Conditions	Yield
In benzene at 20℃; for 24h; Product distribution; Further Variations:; Reaction partners; Solvents; reaction times;
With hydrogenchloride In acetic acid methyl ester; water at 20 - 23℃; for 4.5h; Temperature; Concentration; Solvent;

...Expand

: 116-11-0
2-Methoxypropene

: 81496-81-3
dihydroartesiminin

: 71963-77-4
artemether

Conditions

Conditions	Yield
Stage #1: 2-Methoxypropene; dihydroartesiminin In methanol at 20℃; for 0.25h; Stage #2: With methanesulfonyl chloride In methanol at 10 - 20℃; Stage #3: With sodium hydrogencarbonate In methanol at 20℃; for 2h; Product distribution / selectivity;

: 77-76-9
2,2-dimethoxy-propane

: 81496-81-3
dihydroartesiminin

: 71963-77-4
artemether

Conditions

Conditions	Yield
Stage #1: 2,2-dimethoxy-propane; dihydroartesiminin In methanol at 20℃; for 0.25h; Stage #2: With chloro-trimethyl-silane In methanol at 10 - 20℃; Stage #3: With sodium hydrogencarbonate In methanol at 20℃; for 2h; Product distribution / selectivity;

: 1445-45-0
Trimethyl orthoacetate

: 81496-81-3
dihydroartesiminin

: 71963-77-4
artemether

Conditions

Conditions	Yield
Stage #1: Trimethyl orthoacetate; dihydroartesiminin With sulfuric acid In methanol Stage #2: With sulfuric acid In methanol Stage #3: With sodium hydrogencarbonate In methanol; water Product distribution / selectivity;
With boron trifluoride diethyl etherate In methanol at 10 - 20℃; for 4h;	98 g

: α-artemether

: 71963-77-4
artemether

Conditions

Conditions	Yield
With chloro-trimethyl-silane In toluene at 25 - 30℃; for 12h;

: 67-56-1
methanol

: 81496-81-3
dihydroartesiminin

A: 71963-77-4
artemether

B: α-artemether

Conditions

Conditions	Yield
Stage #1: dihydroartesiminin With dodecatungstophosphoric acid hydrate In dichloromethane at 20℃; for 0.0833333h; Stage #2: methanol In dichloromethane at 20℃; for 3h; optical yield given as %de;

...Expand

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

A: 71963-77-4
artemether

B: α-artemether

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate / methanol 2.1: dodecatungstophosphoric acid hydrate / dichloromethane / 0.08 h / 20 °C 2.2: 3 h / 20 °C View Scheme

: 67-56-1
methanol

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

A: 71963-77-4
artemether

B: α-artemether

Conditions

Conditions	Yield
With sodium tetrahydroborate; cellulose sulfuric acid; trimethyl orthoformate In tetrahydrofuran at -5 - 20℃; for 2.5h;	A n/a B n/a

...Expand

: 67-56-1
methanol

: 71939-50-9
dihydroartemisinin

: 71963-77-4
artemether

Conditions

Conditions	Yield
With amberlyst-15 In 2-methyltetrahydrofuran at 20℃; for 4h; Kinetics; Reagent/catalyst; Temperature; Flow reactor;

: 67-56-1
methanol

: 71939-50-9
dihydroartemisinin

: 71963-77-4
artemether

Conditions

Conditions	Yield
With perchloric acid In dichloromethane at 30 - 38℃; for 0.166667h; Temperature; Large scale;	756 g

: 1445-45-0
Trimethyl orthoacetate

: 63968-64-9
C12H13O2(CH3)3(O)(OO)

: 71963-77-4
artemether

Conditions

Conditions	Yield
Stage #1: C12H13O2(CH3)3(O)(OO) With methanol; sodium tetrahydroborate at -10 - -5℃; for 3h; Stage #2: Trimethyl orthoacetate With sulfuric acid; boron trifluoride diethyl etherate In methanol at 20℃; for 4h; pH=6 - 8; Catalytic behavior; Temperature;	101.9 g

: 71963-77-4
artemether

: deoxy-β-artemether

Conditions

Conditions	Yield
With zinc In acetic acid for 1h; Ambient temperature;	72%

: 71963-77-4
artemether

A: 9α-acetoxy-10β-methoxyartemethin-I

B: 3α-hydroxydeoxydihydroqinghaosu

C: 3α-hydroxy-12β-methoxyartemethin-III

Conditions

Conditions	Yield
With iron(II) sulfate In water; acetonitrile at 37℃;	A 37% B 4% C 44%

...Expand

: 10318-18-0
DL-cysteine hydrochloride

: 71963-77-4
artemether

A: 9α-acetoxy-10β-methoxyartemethin-I

B: 3α-hydroxy-12β-methoxyartemethin-III

C: Acetic acid (1R,3S,4R,4aS,7R,8S,8aR)-8-ethyl-8a-hydroxy-3-methoxy-4,7-dimethyl-octahydro-isochromen-1-yl ester

D: 3-[2-((1R,3S,4R,4aS,7R,8S,8aR)-1-Acetoxy-8a-hydroxy-3-methoxy-4,7-dimethyl-octahydro-isochromen-8-yl)-ethylsulfanyl]-2-amino-propionic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate; iron(II) sulfate In acetonitrile at 20℃; for 4h; Further byproducts given;	A 26% B 44% C 10% D 3.2%

...Expand

: 71963-77-4
artemether

: 1,4-diacetylbenzene bis(trimethylsilyl) enol ether

: 10-m-acetylphenylartemisinin dimer

Conditions

Conditions	Yield
Stage #1: artemether With titanium tetrachloride In dichloromethane at -78℃; for 0.0833333h; Metallation; Stage #2: 1,4-diacetylbenzene bis(trimethylsilyl) enol ether In dichloromethane at -78℃; for 1h; Condensation;	33%

: 71963-77-4
artemether

A: 3α-hydroxydeoxy-β-artemether

B: 2-[(R)-4-Methyl-2-oxo-3-(3-oxo-butyl)-cyclohexyl]-propionaldehyde

C: 9α-acetoxy-10β-methoxyartemethin-I

Conditions

Conditions	Yield
With iron(II) chloride In acetonitrile for 0.0333333h; Ambient temperature;	A 23% B 16% C 32%

...Expand

: 71963-77-4
artemether

: 183060-22-2
1,4-diacetylbenzene bis(trimethylsilyl) enol ether

: 229981-82-2
10-p-acetylphenylartemisinin dimer

Conditions

Conditions	Yield
Stage #1: artemether With titanium tetrachloride In dichloromethane at -78℃; for 0.0833333h; Metallation; Stage #2: 1,4-diacetylbenzene bis(trimethylsilyl) enol ether In dichloromethane at -78℃; for 1h; Condensation;	26%

: 10318-18-0
DL-cysteine hydrochloride

: 71963-77-4
artemether

: C18H29NO6S

Conditions

Conditions	Yield
With sodium hydrogencarbonate; iron(II) sulfate In acetonitrile at 20℃; for 4h;	1.4%

: 32195-55-4
Mn(TPP)Cl

: 71963-77-4
artemether

: Acetic acid (1R,3S,4R,4aS,7R,8S,8aR)-8a-hydroxy-3-methoxy-4,7-dimethyl-8-[2-((4Z,10Z,15Z,19Z)-(S)-5,10,15,20-tetraphenyl-2,3,22,24-tetrahydro-porphin-2-yl)-ethyl]-octahydro-isochromen-1-yl ester

Conditions

Conditions	Yield
With tetra(n-butyl)ammonium borohydride; cadmium(II) nitrate 1.) CH2Cl2, r.t., 1 h, 2.) CH2Cl2, DMF, 30 min; Yield given. Multistep reaction;

: 71963-77-4
artemether

A: 1356857-18-5
β-2-deoxy-9-epidihydroartemisinin

B: 107466-88-6
(2S, 3R, 6S)-2-(3-oxobutyl)-3-methyl-6-<(R)2-propanal>-cyclohexanone

C: 72807-92-2
deoxydihydroqinghaosu

Conditions

Conditions	Yield
With 1-Benzyl-1,4-dihydronicotinamide; lumiflavin In acetonitrile at 20℃; for 2.5h; pH=7.4; aq. phosphate buffer; Inert atmosphere;

...Expand

: 71963-77-4
artemether

A: 1356857-18-5
β-2-deoxy-9-epidihydroartemisinin

B: 72807-92-2
deoxydihydroqinghaosu

Conditions

Conditions	Yield
With 1-Benzyl-1,4-dihydronicotinamide; riboflavin In acetonitrile at 20℃; for 3h; pH=7.4; aq. phosphate buffer; Inert atmosphere;	A 52 %Spectr. B 12 %Spectr.

: 71963-77-4
artemether

A: 9α-acetoxy-10β-methoxyartemethin-I

B: 3α-hydroxy-12β-methoxyartemethin-III

Conditions

Conditions	Yield
With oxygen; methylene blue; ascorbic acid In acetonitrile at 20℃; for 24h; pH=7.4; aq. phosphate buffer;

Artemether Specification

1. Introduction of Artemether

Artemether is one kind of white crystals or a white, crystalline powder. The chemical name of Artemether is (3R,5aS,6R,8aS,9R,10S,12R,12aR)-Decahydro-10-methoxy-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin. The Product Categories of this chemical is Antimalarial. Artemether is toxic. It is flammable. It will produce Stimulate smoke when buring. So the storage environment should be ventilate, low-temperature and dry.

2. Properties of Artemether

Physical properties about Artemether are:
(1)Boiling Point: 358 °C; (2)Flash Point: 141 °C; (3)Density: 1.18 g/cm³; (4)Index of Refraction: 1.518; (5)Molar Refractivity: 76.54 cm³; (6)Molar Volume: 252.5 cm³; (7)Surface Tension: 39.9 dyne/cm; (8)XLogP3-AA: 3.1; (9)H-Bond Acceptor: 5; (10)Rotatable Bond Count: 1; (11)Exact Mass: 298.178024; (12)MonoIsotopic Mass: 298.178024; (13)Topological Polar Surface Area: 46.2; (14)Heavy Atom Count: 21.

3. Structure Descriptors of Artemether

(1) Canonical SMILES: CC1CCC2C(C(OC3C24C1CCC(O3)(OO4)C)OC)C;
(2) Isomeric SMILES: C[C@@H]1CC[C@H]2[C@H]([C@H](O[C@H]3[C@@]24[C@H]1CC[C@](O3)(OO4)C)OC)C;
(3) InChI: InChI=1S/C16H26O5/c1-9-5-6-12-10(2)13(17-4)18-14-16(12)11(9)7-8-15(3,19-14)20-21-16/h9-14H,5-8H2,1-4H3/t9-,10-,11+,12+,13+,14-,15-,16-/m1/s1;
(4) InChIKey: SXYIRMFQILZOAM-HVNFFKDJSA-N.

4. Toxicity of Artemether

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intramuscular	263mg/kg (263mg/kg)	BEHAVIORAL: FOOD INTAKE (ANIMAL) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. Vol. 2, Pg. 138, 1981.
mouse	LD50	oral	1gm/kg (1000mg/kg)		Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. Vol. D13, Pg. 280, 1992.
mouse	LD50	subcutaneous	390mg/kg (390mg/kg)		Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. Vol. D13, Pg. 280, 1992.

5. Safety information of Artemether

Poison by intramuscular route. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes.

6. Uses of Artemether

Artemether is an antimalarial used for the treatment of multi-drug resistant strains of falciparum malaria. Arteether is the derivative of artemisinin, it is a strong schizonticide and can take rapid control of symptoms by killing plasmodium, it is much more effective than artemisinin and used for the curative treatment of all kinds of malaria, especially for the cerebal malaria , severe malaria and chloroquine-resistant malaria. It is also applied in combination with lumefantrine in clinical treatments of malaria.

Product Name

Artemether

Synthetic route

Artemether Specification

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